【结 构 式】 |
【分子编号】59789 【品名】2,6-di(tert-butyl)-4-(dimethoxymethyl)phenol 【CA登记号】 |
【 分 子 式 】C17H28O3 【 分 子 量 】280.40752 【元素组成】C 72.82% H 10.06% O 17.12% |
合成路线1
该中间体在本合成路线中的序号:(IX)An improved synthesis has been reported. Acid-catalyzed ketalization of aldehyde (VIII) with trimethyl orthoformate provided the dimethyl acetal (IX) which, upon thermal decomposition in refluxing xylene, gave rise to the alpha-methoxy methylenequinone derivative (X). This was then condensed with the lithio derivative of sultam (III) to form selectively the desired E-adduct. In an analogous procedure, aldehyde (VIII) was converted to the chloromethylene compound (XI) with methanesulfonyl chloride and triethylamine in refluxing CH2Cl2. Condensation of (XI) with the lithiated sultam (III) furnished the desired E-benzylidene sultam.
【1】 Inagaki, M.; Haga, N.; Kobayashi, M.; Ohta, N.; Kamata, S.; Tsuri, T.; Highly E-selective and effective synthesis of antiarthritic drug candidate S-2474 using quinone methide derivatives. J Org Chem 2002, 67, 1, 125. |
【2】 Haga, N.; Inagaki, M.; Matsumoto, S.; Kamata, S. (Shionogi & Co. Ltd.); Method for producing benzylidene derivs.. EP 0626377 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(III) | 59785 | 2-ethyl-1lambda~6~-isothiazolidine-1,1-dione | C5H11NO2S | 详情 | 详情 | |
(VIII) | 14875 | 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde; 3,5-di(tert-butyl)-4-hydroxybenzaldehyde; 3,5-Di-tert-butyl-4-hydroxybenzaldehyde | 1620-98-0 | C15H22O2 | 详情 | 详情 |
(IX) | 59789 | 2,6-di(tert-butyl)-4-(dimethoxymethyl)phenol | C17H28O3 | 详情 | 详情 | |
(X) | 59790 | 2,6-di(tert-butyl)-4-(methoxymethylene)-2,5-cyclohexadien-1-one | C16H24O2 | 详情 | 详情 | |
(XI) | 59791 | 2,6-di(tert-butyl)-4-methylene-2,5-cyclohexadien-1-one | C15H22O | 详情 | 详情 |